1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose

Base Information

• Chemical Name: 1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose
• CAS No.: 5115-74-2
• Molecular Formula: C₁₄H₁₉NO₆S
• Molecular Weight: 329.374
• DSSTox Substance ID: DTXSID801311264
• Wikidata: Q27098294
• Mol file: 5115-74-2.mol

Synonyms:1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose;Desulfobenzylglucosinolate;CHEBI:15911;DTXSID801311264;5115-74-2;Q27098294;[(2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)oxan-2-yl] N-hydroxy-2-phenylethanimidothioate

Chemical Property of 1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose

Chemical Property:

• PSA: 148.04000
• LogP: -0.45010
• XLogP3: 0.4
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 329.09330850
• Heavy Atom Count: 22
• Complexity: 376

Purity/Quality:

DESULFOGLUCOTROPAEOLIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(=NO)SC2C(C(C(C(O2)CO)O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)CC(=NO)S[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O

Technology Process of 1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose

There total 6 articles about 1-S-(N-hydroxy-2-phenylethanimidoyl)-1-thio-beta-D-glucopyranose which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 69.0%

Phenylacetothiohydroxamic Acid (10593-79-0) + uridine 5'-diphosphoglucose disodium salt (6858-46-4,7333-33-7,14656-80-5,28053-08-9,53829-41-7,108320-88-3,137868-52-1) → benzyl desulphoglucosinolate (5115-74-2,5115-75-3)

Guidance literature:

With DL-dithiothreitol; calf intestine alkaline phosphatase; UDP-glycosyltransferase 74B₁ from Arabidopsis thaliana; In aq. phosphate buffer; dimethyl sulfoxide; at 37 ℃; for 2h; pH=7; Kinetics; Darkness; Enzymatic reaction;

DOI:10.1039/c6ob01003b

Reference yield:

→ benzyl desulphoglucosinolate (5115-74-2,5115-75-3)

Guidance literature:

With ammonia;

DOI:10.1021/ja01564a066

Reference yield:

Phenylacetaldehyde oxime (7028-48-0) → benzyl desulphoglucosinolate (5115-74-2,5115-75-3)

Guidance literature:

Multi-step reaction with 3 steps

1: N-chloro-succinimide / N,N-dimethyl-formamide / 0.5 h / 0 °C / Darkness; Inert atmosphere

2: triethylamine; sodiumsulfide nonahydrate / water; diethyl ether / 14 h / 20 °C / Darkness; Inert atmosphere

3: UDP-glycosyltransferase 74B₁ from Arabidopsis thaliana; DL-dithiothreitol; calf intestine alkaline phosphatase / aq. phosphate buffer; dimethyl sulfoxide / 2 h / 37 °C / pH 7 / Darkness; Enzymatic reaction

With N-chloro-succinimide; sodiumsulfide nonahydrate; DL-dithiothreitol; calf intestine alkaline phosphatase; UDP-glycosyltransferase 74B₁ from Arabidopsis thaliana; triethylamine; In aq. phosphate buffer; diethyl ether; water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1039/c6ob01003b

upstream raw materials:

Phenylacetothiohydroxamic Acid

uridine 5'-diphosphoglucose disodium salt

Phenylacetaldehyde oxime

phenylacetaldehyde

Refernces

• 1、 Marroun, Sami,Montaut, Sabine,Marquès, Stéphanie,Lafite, Pierre,Coadou, Ga?l,Rollin, Patrick,Jousset, Guillaume,Schuler, Marie,Tatibou?t, Arnaud,Oulyadi, Hassan,Daniellou, Richard. "UGT74B1 from Arabidopsis thaliana as a versatile biocatalyst for the synthesis of desulfoglycosinolates". . p. 6252 - 6261. Retrieved 2016/07/11.